Catalytic enantioselective Minisci-type addition to heteroarenes

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Science  27 Apr 2018:
Vol. 360, Issue 6387, pp. 419-422
DOI: 10.1126/science.aar6376

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Light and acid steer a radical addition

So-called Minisci reactions have been used for decades in pharmaceutical and agrochemical synthesis to make carbon-carbon bonds. The reactions link carbon radicals to the carbon centers adjacent to nitrogen in pyridine rings. Proctor et al. devised a method to steer these reactions to just one of two possible mirror-image products. To make the radicals, they prepared derivatives of widely available amino acids and then activated them with an iridium photocatalyst. At the same time, a chiral phosphoric acid catalyst was used to activate the pyridine and bias the reaction geometry.

Science, this issue p. 419